Summary
Living in Springfield, the home ofThe Simpsonsfamily, might seem like a good time at first. Yet even though the city looks peaceful on the surface, not all of its residents are friendly. A fair number of them have committed more than one crime or are just plain bad people, sometimes both, which makes it difficult for Homer, Marge, Bart, Lisa, and Maggie to get along with them.
It doesn’t help matters that the police department in Springfield, led by Sheriff Wiggum, is usually lax and tends to do more harm than good. In the end, it’s up to the Simpsons and their friends and neighbors to deal with the evilest characters on the show.
4Sideshow Bob
Driven To Kill Bart & Threatened To Drop An Atomic Bomb
Unlike Mr. Burns, who uses his money and connections to stay out of trouble and avoid punishment for his actions, Sideshow Bob has been sentenced and imprisoned multiple times. Yet it doesn’t stop him from escaping and wreaking havoc all over again.Bob’s longtime nemesis is Bart,who first got him sent to prison when he found out that Bob had impersonated Krusty and framed him for a robbery. Since then, Bob hasattempted to kill Bartmany times and committed other crimes as well, such as marrying Selma and trying to murder her, or destroying the television.
He tends to fail in his attempts due to the work of Bart and others. What makes Sideshow Bob a slightly redeemable character is the fact that when he finally has the chance to kill Bart and there is no way Bart can stop him, he realizes he cannot do it. At one point, Bob also starts a new life in Italy and builds a family… until Bart and the rest of his family arrive and ruin it for him.
3Kang And Kodos
Invasion In Progress
Even thoughThe Simpsonsis more grounded in reality than other shows by Matt Groening likeFuturamaandDisenchanted, it still contains sci-fi and fantasy elements. One example is Kang and Kodos, the two alienswho attempt to invade Earthmultiple times in the Treehouse of Horror episodes. Over the years, they come up with many sinister plans. One time, Kang, masked as Bill Clinton, was elected president.
They enjoy watching the Earth suffering from afar as well, such as when a zombie apocalypse erupts. Overall, even though their characters change from one episode to the next, Kang and Kodos are antagonistic more often than not, and generally have no good intentions for Springfield.
2Fat Tony
Mob Boss
There has been more than one character with this same nickname inThe Simpsons. The original Fat Tony wasthe head of the mafiain Springfield. For Tony, crime was business, and while he did despicable things, he was purely motivated by money, unlike some other characters on this list.
Tony also preferred not to get his hands dirty and delegated work to his men, even though he wasn’t afraid to step into action. For example, he has put out contracts to kill both the mayor and Homer on separate occasions. Yet he also worked with Homer when Homer hired him to intimidate Marge’s business rivals. Tony later died and his cousin of the same name replaced him, continuing the character’s legacy of crime.
1Montgomery Burns
The Quintessential Antagonist
Mr. Burns is a personification of the old saying that money ruins character. He’s filthy rich, but also cold, calculating, distant, merciless, greedy, and the list goes on. The only person who genuinely seems to care about him is his assistant, Waylon Smithers, who’s in love with Mr. Burns. Burns doesn’t return Smithers' feelings, however, ashe proved in multiple episodeswhen he fell for different women, including Marge Simpson. Burns has very little respect or love for his employees, and when he decides he doesn’t like somebody, he sacks them on the spot, regardless of the cause (to be fair, Homer does cause several catastrophes that threaten the nuclear plant and all of Springfield for that matter).
Burns also doesn’t shy away from gaining control over the media to write positive articles about him and intimidates Lisa to give up publishing her critical newspaper. Another time, he injures Bart in a hit-and-run and doesn’t care what happens to the boy. He also poisons the local waters, which leads to the fish mutating, tries to kill Bart, Homer, and Abe Simpson, andso much more.Several episodes make an effort to humanize Burns, but while it’s possible to understand where he’s coming from, it doesn’t change the fact that nobody likes him. So much so that when Maggie shoots him, nobody seems to be stricken about it, except for Smithers.
